Bumetanide

Bumetanide

Clinical data
Trade names	Bumex
AHFS/Drugs.com	Monograph
MedlinePlus	a684051
Pregnancy category	AU: B3 US: C (Risk not ruled out)
Routes of administration	oral, intravenous, intramuscular
ATC code	C03CA02 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	almost complete (~80%)
Protein binding	97%
Metabolism	hepatic
Biological half-life	~0.8 hours
Excretion	renal
Identifiers
IUPAC name 3-butylamino-4-phenoxy-5-sulfamoyl-benzoic acid
CAS Number	28395-03-1 Y
PubChem (CID)	2471
IUPHAR/BPS	4837
DrugBank	DB00887 Y
ChemSpider	2377 Y
UNII	0Y2S3XUQ5H Y
KEGG	D00247 Y
ChEBI	CHEBI:3213 Y
ChEMBL	CHEMBL1072 Y
ECHA InfoCard	100.044.534
Chemical and physical data
Formula	C17H20N2O5S
Molar mass	364.417 g/mol
3D model (Jmol)	Interactive image
SMILES O=S(=O)(c2cc(cc(NCCCC)c2Oc1ccccc1)C(=O)O)N
InChI InChI=1S/C17H20N2O5S/c1-2-3-9-19-14-10-12(17(20)21)11-15(25(18,22)23)16(14)24-13-7-5-4-6-8-13/h4-8,10-11,19H,2-3,9H2,1H3,(H,20,21)(H2,18,22,23) Y Key:MAEIEVLCKWDQJH-UHFFFAOYSA-N Y

Bumetanide (trade names Bumex or Burinex) is a loop diuretic of the sulfamyl category to treat heart failure. It is often used in people in whom high doses of furosemide are ineffective. It is marketed by Hoffmann-La Roche. The main difference between the two substances is in bioavailability and pharmacodynamic potency. Furosemide is incompletely absorbed in the intestine (60%), and there are substantial inter- and intraindividual differences in bioavailability (range 10-90%). Bumetanide is almost completely absorbed (80%), and the absorption is not altered when it is taken with food. It is said to be a more predictable diuretic, meaning that the predictable absorption is reflected in a more predictable effect.

Bumetanide is 40 times more potent than furosemide for patients with normal renal function.

In the brain, bumetanide blocks the NKCC1 cation-chloride co-transporter, and thus decreases internal chloride concentration in neurons. In turn, this concentration change makes the action of GABA more hyperpolarizing, which may be useful for treatment of neonatal seizures, that quite often are not responsive to traditional GABA-targeted treatment, such as barbiturates. Bumetanide is therefore currently under evaluation as a prospective antiepileptic drug.

On October 24, 2008, ESPN reported a number of NFL players were being suspended under the steroid policy as a result of taking bumetanide. The drug is often used for weight loss, but also to mask other drugs or steroids by helping to dilute the contents of the user's urine, yielding a lower concentration of filtered substances which may then go undetected.

Bumetanide was an undisclosed active ingredient in the over the counter weight loss supplement StarCaps. StarCaps was pulled off the market after the presence of the undisclosed ingredient was discovered by the Food and Drug Administration.